📚 auntie jenn Part 5 of 6
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MATURE SEX

Auntie Jenn Ch 05

Auntie Jenn Ch 05

by jaymie_dee
20 min read
4.44 (6800 views)
adultfiction

Of Virginity and Disaster

For the next two weeks, Auntie and I would get together every night in one of our bedrooms. Much to my delight, she wore a variety of babydoll nighties in various colors that never failed to arouse and excite me.

And every night we managed to discover new and creative ways to provoke and excite one another toward mutual masturbation and orgasm. We often watched porn videos together to set the sensual tone of the evening and showed one another the videos that personally aroused us the most.

Auntie was rather fond of the massage room videos, and it didn't seem to matter to her if the couples were heterosexual or Lesbian. I was greatly excited by her massage videos as well, especially those that featured an actress known as Rita Peach. Rita had a way of bringing her partner to orgasm with such warmth, sensuality, and tenderness that never failed to arouse and excite us both.

I showed her several videos, many featuring an actress named Karina Hart--a woman with beautiful large breasts and an apparent enthusiasm for masturbation in a variety of ways. I especially enjoyed seeing her reach orgasm, watching as her body twitched and shuddered in much the same manner Auntie's body did when she reached orgasm, with her thigh muscles trembling uncontrollably.

Karina's videos led to a discussion of women's breasts when Auntie commented that it appeared to her that I seemed to be particularly fond of big-breasted women.

When I readily admitted that I was attracted to busty women, Auntie laughingly disclosed that Karina Hart's breasts left her feeling slightly inadequate, to which I disagreed adamantly. While I had never seen Auntie's breasts, I could certainly gauge their size and weight from the heavy sway beneath her nighties, and I told her so.

Without even a hint of nervousness or embarrassment, Auntie bared her breasts to me for the first time that night, raising the front of her nightie to her neck. Once again, I'm sure my eyes bulged like those proverbial cartoon characters when she did so. Seeing her breasts for the first time was enough to take my breath away and, despite her protests to the contrary, they were large, perhaps not quite as large as Karina's but beautifully big and nicely formed without even a hint of sag for a woman her age. When asked she readily revealed she wore a D-cup bra.

She also allowed me to touch her breasts that night, a sensual experience that gave me such an urgent erection that, to Auntie's delight, I began stroking myself immediately with my free hand.

One night after our mutually satisfying orgasms, I asked if she would allow me to feel how wet she was between her legs. She smiled coyly and I could see she was weighing the consequences of such a personally private intimacy between us before tacitly nodding her head.

She took my hand in hers and guided me down between her legs, parting them to allow me access. To my astonishment, her entire labia was copiously slick and wet and the heat between her legs almost made me gasp aloud. With a tentative smile, she closed her thighs together, holding my hand in place.

I was instantly urgently erect once more even though it had only been less than five minutes since my previous orgasm. Visions of lying with her and penetrating those slick wet folds were more than enough to drive me over the edge and out of my mind. Auntie's eyes widened as she saw my urgent need rising and she gently pulled my hand from between her legs.

"I think maybe we should tone down this kind of personal intimacy, honey," she said. "From your reaction, I think you just might like it a little too much... and so do I."

"But, it's not such a bad thing--Is it?" I countered, acutely aware of how her slick vaginal secretions still saturating my fingers. "I mean... we could maybe even use our hands to masturbate each other sometimes. What would be the harm in that?"

She took my face in her hands and looked deeply into my eyes. "But there IS harm in it, honey," she said softly, her eyes imploring. "Because I know in my heart that I would like it WAY too much... and then I would want even more of that kind of personal intimacy with you... and I'm not willing to go down that path. It's too much of a slippery slope toward real incest."

I nodded, understanding her concerns and realizing that I too would want things to continue to escalate.

"As much as I would LOVE to have sex with you, Jamie, I can't allow it to happen. It would be such a betrayal to my sister... I just can't go there."

Again I nodded, thankful for even the relatively tame intimacies we had been able to share.

Our tamer intimacies did, however, become a little more elevated in that we seemed to gradually graduate toward being more and more affectionate with one another. Occasionally I would hold her in my arms, urging her toward orgasm--my lips near her ear--as her hand moved between her legs. "Cum for me, Auntie... Let it go," I would breathe softly as I gently cupped and caressed her breast.

Despite the elevated affection for one another, we both recognized the danger of proceeding beyond her personal boundaries. And, while I'm sure I could have easily been persuaded further, I tempered my lustful enthusiasm for Auntie's sake and respected the limitations she had imposed on our intimacies.

****************************************************************

One evening, as Auntie and I lay side by side on my bed, our shoulders and hips gently touching, holding hands as we conversed softly, content in the warm intimacy of each other's company.

"How old were you when you had sex for the first time?" I asked, secretly hoping against hope that I wasn't the only soon-to-be twenty-year-old virgin to have ever lived.

She pursed her lips thoughtfully, "Let's see... I was eighteen, so that would have been 1991." She laughed softly, "Ronnie James... at the drive-in theater... in the back seat of his car." She laughed again, "God, I haven't thought about Ronnie in a hundred years."

"Was it nice though... your first time?" I asked, resigning myself to already being almost two years older than she had been.

"Not... totally," she said, sighing heavily. "I don't remember much about it other than it hurt a lot, and I bled a bit too." She laughed softly, "God, he was SO pissed at me for getting blood on his back seat. He and I only did it that one time, I think he moved on to girls with more experience."

"Ouch, sorry," I said.

She waved a hand in the air dismissively, "Water under the bridge now," she said. "And, what about you, who was your first?"

When I paused, not wishing to reveal my little secret, Auntie's eyes suddenly widened and she smiled, "I bet it was that little Asian girl you brought home to dinner. What was her name?"

"Linda," I responded, knowing immediately whom she meant..

"That's right... Linda," said Auntie, snapping her fingers. "I kind of liked her, she was pretty, and the two of you were cute together. Was she your first?"

I shook my head, hoping Auntie would change the subject.

"No? Not her? So who was your first then?"

I took a deep breath and bit my lip, "Um... well..."

Auntie gasped aloud, rolling onto her side to look at me with wide eyes, "Oh, my God, Jamie!" she said softly, "You've never?"

I shrugged sheepishly, the cat being out of the proverbial bag.

"I'm a little astonished by that, Jamie," she said, her brow furrowed. "I mean... throughout high school, you never seemed to be without female companionship. You always seemed to have a girlfriend."

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"I know," I responded with disappointment, "I guess I've always felt... I don't know... a little intimidated by those girls. And the timing just never felt right either. I didn't own a car... and I couldn't invite a girl home to my bedroom, Mom would've had a cow."

Auntie laughed a little sadly at my dilemma, reaching over to tenderly stroke my cheek with her hand. "It's okay, though, Jamie. It really is. When the time is right it'll happen for you."

I sighed and shrugged, "Yeah, I suppose. Some of the guys used to drive out to the Chicken Ranch brothel up near Pahrump and I had been thinking that might be the best way to go for me.

Auntie frowned and shook her head, "I guess that would solve the problem of your virginity, but I seriously doubt it would have been the 'best way', as you put it."

She paused thoughtfully before continuing, "Don't forget, everyone always remembers their first time. It's like tonight with Ronnie James for me. Ideally, you want that first experience to at least be pleasantly memorable, and not just with some nameless, faceless prostitute."

I nodded, what she said made perfect sense. "I don't suppose you'd be willing to help me un-virgin myself, right?"

Auntie's smile vanished and she shook her head, "Oh, honey... That's a place you and I should never go. I mean, it's one thing for us to play around sexually and tease each other, but actually having sex with my little sister's son is the literal definition of incest, and I'm not willing to cross that line."

I nodded, wishing it wasn't so. I personally felt no great stigma about incest. I could easily have sex with Auntie Jenn, and the idea of it being incestuous wouldn't bother me at all.

An idea suddenly occurred to me right at that moment, and my eyes widened. "Auntie?" I queried, looking into her eyes. "What if we didn't have sex... what if I just went inside for just a few seconds... you know... just to experience what it feels like to be inside a woman?"

Auntie frowned and bit her lip, and I could see she was weighing the situation in her mind. "I'm... not sure that would be such a good idea, honey. There's just too much that can go wrong."

"But it would just be for maybe less than a minute... only a few seconds," I went on in an enthusiastic rush, "I would just go inside you, feel what it's like, and then pull myself right back out again."

Auntie shook her head skeptically, but I could see she was still not denying the possibility out of hand.

"And," I continued hopefully, "I promise... it won't be anything more than that. For sure, I won't cum inside you, Auntie. It will all be over way before anything like that would ever happen."

"You think that's how it will be?" said Auntie, the corners of her mouth curling slightly into a smile. "Just in and out and nothing more? You won't cum inside me?"

"Of course not," I responded, slightly offended she would doubt me. "I ONLY want to see how it feels to be inside a woman."

"You promise you won't cum inside me?" she said, her smile widening.

"Absolutely," I said with enthusiasm sensing her resolve was weakening.

"All right," she said, her smile strangely widening, "As long as you can promise me that you'll only go inside me for a few seconds, and then pull yourself out without cumming inside me... If you can promise me that, then I suppose I'll allow it."

I almost gasped. Holy shit! It was really going to happen. I watched in fascination as Auntie parted her legs and began to touch herself.

"I'm still very wet, honey... make yourself hard again for me," she said softly.

I needed absolutely no encouragement, the mere thought of lying between Auntie's gorgeous legs and penetrating her was enough to make me urgently hard.

She lay back and parted her legs wide for me as I insinuated myself between them. I looked down at her vulva, her labial lips glistening slickly, and realized that I had no idea exactly where the entrance to her vagina was.

Sensing my insecurity, she raised her hands to me, "Don't worry, honey, I'll guide you," she said.

I lay forward and she grasped my erection gently, guiding me to her vagina. She moved the tip of my cock over her lips, making me slick with her secretions. I pressed forward feeling the tip of my cock part her lips... felt the heat of her vagina and then slowly began to penetrate her.

Never in my wildest fantasies had I ever anticipated the exquisite physical sensation of a woman's vagina. As I began to slide into her, the muscles of her vaginal walls seemed to caress me tightly as if urging me deeper. To my complete astonishment, the exquisitely overwhelming sensation of her warm wet vagina brought me instantaneously to the brink of orgasm.

"Oh!" I gasped, holding myself completely still inside her, sensing that even the slightest of movements would precipitate my orgasm. I looked down at Auntie, my eyes wide with anguish, and was surprised to see her smiling up at me sadly.

Her hands moved tenderly over my back and down over my buttocks, cupping my cheeks to hold me firmly as she raised her hips to meet mine and pulled me deeply into her.

I cried aloud, still trying to hold myself perfectly still, but her movement beneath me sent me completely over the edge. With my eyes wide with surprise, my first ejaculation erupted into her.

Auntie grasped my buttocks and pulled me tightly to her. My orgasm was like an unstoppable freight train, I could do nothing to stop it. I held myself completely motionless, resisting the urge to thrust, and STILL my penis pulsed... and pulsed... and pulsed inside her, sending stream after stream of my semen deep into her vagina.

With my eyes still wide with shock and surprise, I looked down into Auntie's eyes and was astonished to see her still smiling up at me sweetly, her hands still grasping my buttocks cheeks to hold me tightly against her.

As my final ejaculation sent the last of my semen into her, I shook my head. "Oh, God, Auntie... Oh, God, I'm SO sorry. I didn't... I didn't..."

Auntie smiled and nodded, "Shhh... " she said, "It's all right, honey. It's all right."

She didn't seem in the least bit upset that I had just reneged on the promise I had made her. And then it hit me. Somehow she knew it was going to happen... and she still allowed it.

"I tried not to, Auntie," I said, "I'm sorry."

She smiled at me warmly, wrapping her arms around my neck to pull me down onto her, my face buried into the nape of her neck.

"I know you tried, honey, I know," she said soothingly as her hands moved tenderly over my back. "I was reasonably sure it would happen for you so quickly."

"You knew? And... still, you let me?"

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"Well... I didn't really know for certain... but because of your inexperience, I thought it might."

"But... " I murmured, the scent of her perfume intoxicating.

"Shhh," she said again, her hands caressing me. "I resisted when you first asked me because I was pretty sure the feeling would overwhelm you. And then... I thought about you going away to school and meeting the pretty girls there. I knew it would only be a matter of time before you finally found yourself in bed with someone you cared for."

"I think I understand, Auntie," I murmured. "You wanted it to happen now, with you."

"I did. With me, you can at least feel reasonably assured that, at my age, I'm not ever likely to become pregnant. But, should it have happened like this with some fertile young California girl, there might surely have been consequences. You were just so smug and self-assured about it, Jamie, I just couldn't let it go. Just in and out, one time, what could possibly go wrong, right?"

"You wanted to show me how wrong I could be?" I said.

Auntie laughed softly, "I thought it might be a wonderfully apropos teaching moment for you, and done in a safe way."

She was absolutely right, I HAD been smugly self-assured about penetrating her just once to see what it felt like. To my credit, though, I had no idea how easily my resolve not to cum could be so easily obliterated by the overwhelming sensuality of not just Auntie's vagina, but most likely ANY woman's vagina.

As I lay on top of her, my penis still deeply penetrated inside her, I was still overwhelmed by the exquisite sensuality of being inside her. I raised my hips slightly, moving inside her, the tight slick walls of her vagina still gripping me pleasurably, and I immediately felt I was close to having another orgasm.

"God, Auntie," I murmured, as I pressed my hips forward to move inside her again, "being inside you like this... is the most beautiful feeling I've ever experienced."

"It feels... very nice... having you inside me too, Jamie," she said. "It actually feels a little TOO nice. So, this might be a very good time for you to pull out."

"God, you feel so good... I think I can cum again, Auntie," I said, giving her another gentle thrust of my hips to excite myself further. "Would it be okay if I did? It feels really close."

"No, Jamie," she said firmly, "You HAVE to stop... this is going too far now."

I heard her words and knew I should do as she wished and pull out of her. But... Oh, God... It just felt so incredibly beautiful inside her, I just couldn't. All I could think of was striving for the orgasm that was only seconds away. Surely she wouldn't mind if I came inside her a second time, right?"

I began thrusting forcefully into her to bring on my orgasm which was tantalizingly only seconds away.

"No, Jamie... NO!" she cried aloud, grasping at my hips in an attempt to push me out of her vagina.

I thrust into her faster, feeling myself cross over the point of no return, my orgasm immanent.

I felt Auntie's body suddenly tense beneath me and her hips beginning to vibrate.

"NO!... STOP, Jamie, PLEASE... I can't... I CAN'T... Oh, God, no... NO!... NO!"

I released into her, sighing in my pleasure. All I could think of at that moment was that surely I was no longer a virgin and I was completely elated.

Auntie cried out with an unintelligible gasp and her hips began to move beneath me, meeting my thrusts with thrusts of her own.

"NoNoNoNoNo... NO!" she gasped, her hips bucking almost frantically. I felt the muscles in her thighs begin to tremble as they had so often done when she reached orgasm.

I couldn't help but smile, knowing she was cumming... and I had made her do it. I was fucking her... and she was cumming. I couldn't help but feel a swell of manly pride at my accomplishment. I kissed her cheek and sighed, "Oh, Auntie, that was SO beautiful."

As her movements stilled, I raised my head with a broad satisfied smile to look down into her eyes.

I jolted, my smile vanishing as I looked down with horror to see the unmitigated look of blind rage in her eyes.

"GET... OFF... OF... ME!" said through her tightly clenched teeth. "Get, OFF, you FUCKING, ASS HOLE!"

I cringed away from her, pulling back to draw my penis from her. As I rose, she lashed out and slapped my face with sufficient force to knock me over.

"How DARE you," she said, her eyes filled with anger, "How fucking DARE you! I begged you to stop, Jamie... I fucking BEGGED you."

"Auntie," I gasped, "Auntie, I'm so sorry."

"You're SORRY?" she responded with a bewildered look, "Well, sorry just isn't going to cut it this time, Jamie... because you can't UN-fuck me."

"It'll never happen again, Auntie, I promise."

"You're god damned right it won't happen again," she said as she slid her legs over the side of the bed and stood up. She glowered down at me as she grasped a handful of tissues, placing them between her legs to staunch the flow of semen.

"I won't happen again because, as of right now, you and I are DONE!" she hissed, turning toward the bedroom door and picking up her robe.

"Can't we talk about this, Auntie?"

She shook her head vehemently, "We're done talking, Jamie. There's nothing more to say, you fucked me. I begged you to stop, but you fucked me anyway. End of story."

With that, she walked out without another word and closed the door behind her.

*******************************************************************

I sat in stunned silence, struggling to process the horribly disastrous turn of events. If it's true, as they say, that one always remembers their first sexual encounter, then surely this was one for the ages. How can I possibly come to terms with a memory that will live with me forever as the most beautiful moment of my life and, at the same time, the worst?

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